2-chloro-6-fluoro-9H-purine | 34792-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-chloro-6-fluoro-9H-purine
• 英文别名: 2-chloro-6-fluoro-7H-purine
• CAS: 34792-98-8
• 化学式: C₅H₂ClFN₄
• 分子量: 172.549
• InChiKey: JIFWWRLWSMVPPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-已烯醛 、 2-chloro-6-fluoro-9H-purine 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  有机催化氮杂-迈克尔加成反应对设计的手性无环核苷酸和无环核苷酸的高度对映选择性合成

  摘要：

  通过非手性嘌呤碱和α，β-不饱和醛的有机催化不对称aza-Michael加成反应合成了手性无环核苷，产率为82-89％，ee高达99％。分离的手性无环核苷易于转化为无环核苷酸。

  DOI：

  10.1002/chem.201100435
• 作为产物：
  描述：

  2-chloro-N,N,N-trimethyl-9H-purin-6-aminium chloride 在 四丁基氟化铵 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以90%的产率得到2-chloro-6-fluoro-9H-purine
  参考文献：
  名称：

  The New Convenient Synthesis of 6-Fluoropurine and Its 7-/9-Unsubstituted Analogues

  摘要：

  6-Fluoropurine and its 7-/9-unsubstituted analogues have good biological activity and serve as important pharmaceutical intermediates. This paper describes a new and convenient synthesis of 6-fluoropurine and its 7-/9-unsubstituted analogues, by first replacing the chlorine atoms with trimethylammonio groups through the reaction of 6-chloropurine and its 7-/9-unsubstituted analogues with trimethylamine, and then replacing the trimethylammonio groups with fluorine atoms using safe and cheap TBAF center dot 3H(2)O as fluorinating agent at room temperature. Compared with reported methods, the new synthesis has milder conditions, shorter reaction times, simpler post-processing and higher (or similar) yields.

  DOI：

  10.3987/com-12-12583

文献信息

• Highly Enantioselective Synthesis of Designed Chiral Acyclonucleosides and Acyclonucleotides by Organocatalytic Aza-Michael Addition
  作者：Hai-Ming Guo、Teng-Fei Yuan、Hong-Ying Niu、Jin-Ying Liu、Run-Ze Mao、De-Yang Li、Gui-Rong Qu

  DOI：10.1002/chem.201100435

  日期：2011.4.4

  Chiral acyclonucleosides were synthesized by an organocatalytic asymmetric aza‐Michael addition reaction from achiral purine bases and α,β‐unsaturated aldehydes in 82–89 % yield and up to 99 % ee. The isolated chiral acyclonucleosides are readily converted to acyclonucleotides.

  通过非手性嘌呤碱和α，β-不饱和醛的有机催化不对称aza-Michael加成反应合成了手性无环核苷，产率为82-89％，ee高达99％。分离的手性无环核苷易于转化为无环核苷酸。
• The New Convenient Synthesis of 6-Fluoropurine and Its 7-/9-Unsubstituted Analogues
  作者：Luoting Yu、Mei Deng、Ningyu Wang、Guangming Xiang

  DOI：10.3987/com-12-12583

  日期：——

  6-Fluoropurine and its 7-/9-unsubstituted analogues have good biological activity and serve as important pharmaceutical intermediates. This paper describes a new and convenient synthesis of 6-fluoropurine and its 7-/9-unsubstituted analogues, by first replacing the chlorine atoms with trimethylammonio groups through the reaction of 6-chloropurine and its 7-/9-unsubstituted analogues with trimethylamine, and then replacing the trimethylammonio groups with fluorine atoms using safe and cheap TBAF center dot 3H(2)O as fluorinating agent at room temperature. Compared with reported methods, the new synthesis has milder conditions, shorter reaction times, simpler post-processing and higher (or similar) yields.